Ruby, RVM, MacPorts and OpenSSL on macOS (Monterey)

This is not so much a blog post but a log for the sake of future Me:

I have been using MacPorts on macOS for many years and am 99% happy with it: it allows installing binary packages and source ones with custom options, allows multiple versions to live side by side, has a lot of packages, can dump the whole list of installed stuff so you can re-install it elsewhere easily and many other things. It’s great.

I have also for a long time used RVM as my ruby version manager of choice. Again, it just works.

An issue with installing older rubies in recent macOS is that the system-provided OpenSSL is version 3, and ruby before 3.1 cannot build against it.

You can get OpenSSL1.0 or 1.1 via MacPorts, but there’s another problem: when you try to install anything recent via MacPorts you will end up with OpenSSL3, and at that point you will have problems building old ruby versions or old versions of gems like eventmachine or puma, expecting to have OpenSSL1.

This problem manifests itself when installing ruby 2.7 via RVM with a build/install log that ends like this

/Users/riffraff/.rvm/src/ruby-2.7.6/lib/rubygems/core_ext/kernel_require.rb:83:in `require': cannot load such file -- openssl (LoadError)
        from /Users/riffraff/.rvm/src/ruby-2.7.6/lib/rubygems/core_ext/kernel_require.rb:83:in `require'
        from /Users/riffraff/.rvm/src/ruby-2.7.6/lib/rubygems/specification.rb:2430:in `to_ruby'
        from ./tool/rbinstall.rb:846:in `block (2 levels) in install_default_gem'
        from ./tool/rbinstall.rb:279:in `open_for_install'
        from ./tool/rbinstall.rb:845:in `block in install_default_gem'
        from ./tool/rbinstall.rb:835:in `each'
        from ./tool/rbinstall.rb:835:in `install_default_gem'
        from ./tool/rbinstall.rb:799:in `block in <main>'
        from ./tool/rbinstall.rb:950:in `block in <main>'
        from ./tool/rbinstall.rb:947:in `each'
        from ./tool/rbinstall.rb:947:in `<main>'

the ruby binary is actually built correctly but the openssl extension failed to build, which you can tell by looking back in the build history

*** Following extensions are not compiled:
         Could not be configured. It will not be installed.
         Check ext/openssl/mkmf.log for more details.

If you look into .rvm/src/ruby-2.7.6/ext/openssl/mkmf.log you will find

/Users/riffraff/.rvm/src/ruby-2.7.6/ext/openssl/extconf.rb:111: OpenSSL >= 1.0.1, < 3.0.0 or LibreSSL >= 2.5.0 is required

So it seems to have ruby use OpenSSL1 you should uninstall OpenSSL3 and everything that depends on it.

FWIW, I think that works, but it’s not ideal.

But fear not! There’s a better solution! You just need to tell RVM (and ruby) to use look for headers and libraries in the right place.

To do this you need to both specify where pkgconfig is and which openssl directories to use.

Luckily, this is not difficult, follow this incantation

$ PKG_CONFIG_PATH=/opt/local/lib/openssl-1.1/pkgconfig rvm reinstall 2.7.6 --with-openssl-lib=/opt/local/lib/openssl-1.1 --with-openssl-include=/opt/local/include/openssl-1.1

You effectively have to tell ruby how to configure itself, and how to find OpenSSL1 at compile time and at link time.

In theory --with-openssl-dir should be enough, but AFAIU MacPorts puts stuff in separate directories which does not play well with ruby-build. Which is fair, as ruby-build does not explicitly support MacPorts, but rather homebrew.

Anyway, once this is solved you may still encounter issues when installing gems that depend on OpenSSL, as those will also need to be told where OpenSSL is.

For example,. this is the error I get installing puma 5.6.4

compiling puma_http11.c
linking shared-object puma/puma_http11.bundle
Undefined symbols for architecture arm64:
  "_SSL_get1_peer_certificate", referenced from:
      _engine_peercert in mini_ssl.o
ld: symbol(s) not found for architecture arm64
clang: error: linker command failed with exit code 1 (use -v to see invocation)
make: *** [puma_http11.bundle] Error 1

make failed, exit code 2

The equivalent error for eventmachine would be something like

linking shared-object rubyeventmachine.bundle
Undefined symbols for architecture arm64:
  "_SSL_get1_peer_certificate", referenced from:
      SslBox_t::GetPeerCert() in ssl.o
ld: symbol(s) not found for architecture arm64
clang: error: linker command failed with exit code 1 (use -v to see invocation)
make: *** [rubyeventmachine.bundle] Error 1

Luckily you the same technique works to install older gems that need OpenSSL1. Notice you need an extra -- to separate the arguments provided to the gem configuration script from the ones to the gem command.

$ PKG_CONFIG_PATH=/opt/local/lib/openssl-1.1/pkgconfig gem install puma -v '5.6.4' -- --with-openssl-lib=/opt/local/lib/openssl-1.1 --with-openssl-include=/opt/local/include/openssl-1.1

(also worth noting: puma 5.6.5 builds without problems, see this and this)

So, hopefully I will be able to forget old code that relies on OpenSSL1 at some point, but in case I need it again: hey future Me, this is how you workaround the issue!

A note on ruby 3.0

If you build ruby 3.0 with MacPorts it will not explode, but it will not build the OpenSSL extesion, in /Users/riffraff/.rvm/src/ruby-3.0.4/ext/openssl/mkmf.log you will find the same error you’ve just seen

/Users/riffraff/.rvm/src/ruby-3.0.4/ext/openssl/extconf.rb:113: OpenSSL >= 1.0.1, < 3.0.0 or LibreSSL >= 2.5.0 is required
	/Users/riffraff/.rvm/src/ruby-3.0.4/ext/openssl/extconf.rb:113:in `<top (required)>'
	./ext/extmk.rb:214:in `load'
	./ext/extmk.rb:214:in `block in extmake'
	/Users/riffraff/.rvm/src/ruby-3.0.4/lib/mkmf.rb:331:in `open'
	./ext/extmk.rb:210:in `extmake'
	./ext/extmk.rb:572:in `block in <main>'
	./ext/extmk.rb:568:in `each'
	./ext/extmk.rb:568:in `<main>'

and this in turn will mean you can’t build puma or eventmachine or other things that depend on the ruby openssl extension

$ gem install puma
ERROR:  While executing gem ... (Gem::Exception)
    OpenSSL is not available. Install OpenSSL and rebuild Ruby (preferred) or use non-HTTPS sources

But you’re good, the same solution as before will allow you to install that version of ruby too

$ PKG_CONFIG_PATH=/opt/local/lib/openssl-1.1/pkgconfig rvm install 3.0 --with-openssl-lib=/opt/local/lib/openssl-1.1 --with-openssl-include=/opt/local/include/openssl-1.1

From ruby 3.1 onwards, ruby will build just fine with the system-provided OpenSSL3, so you will be able to avoid these shenanigans.

You can still build against MacPorts’ version of OpenSSL1 or OpenSSL3 by using the right paths.

Happy hacking future Me!